Triethylamine → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

HRID 618726Notes

Reaction equation

HRID 618726 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:16]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
34 °C

Procedure

To a solution of 4-pyridylcarbinol (50.3 g, 0.46 mol) in methylene chloride (250 mL) under a dry nitrogen atmosphere was added triethylamine (97 mL, 0.69 mol). To this mixture was added dropwise tert-butyl-dimethylsilyl chloride (83.7 g, 0.555 mol) with cooling (T 34° C.). The reaction mixture was stirred overnight at room temperature. The slurry was then filtered and the solvent removed by rotoevaporation. The residue was suspended in toluene and filtered and the solvent removed by rotoevaporation. The residue was suspended in diethyl ether and filtered and the solvent removed by rotoevaporation. The same process was repeated with hexanes to yield 4-t-butydimethylsilyloxymethylpyridine as a brown oil.

Workup

  1. filtrationThe slurry was then filtered
  2. customthe solvent removed by rotoevaporation
  3. filtrationfiltered
  4. customthe solvent removed by rotoevaporation
  5. filtrationfiltered
  6. customthe solvent removed by rotoevaporation

Sources & evidence

ORD record
ord-6a7791a592e4498483fe6789416d7374
Source dataset
uspto-grants-1999_09
Patent number
US05955480

Reaction notes

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